The twentieth century saw capitalist growth accelerating the pace of urban life and transforming cities ever more clearly into sites of uneven and combined development. The result, for novelists, was an intensification of the problem of representing urban form – both as unmappable totality and as subjective experience of fragmentation, distraction and unexpected connection. In line with David Harvey's thesis concerning the 'space-time compression' endemic to modernity, I claim that not only are technological advances in urban transport and communications reflected in the shifting registers of novelistic characters' perception of their environment, but that this change in perception embodies a break with the unilinear logic of sequence and setting to encompass what Ernst Bloch terms 'the synchronicity of the non-synchronous,' or an uneven spatial simultaneity, characteristic of modern fiction. In Part I, by comparing the New York of John Dos Passos' Manhattan Transfer (1925) with the Istanbul of Ahmet Hamdi Tanpınar‘s Huzur (1949), I elucidate the differential stakes of modernist representations of the city, the core and the periphery, as the conjoining of contemporary and archaic forms. In both novels, I argue, the motifs of music and transport function in analogous ways – fragments of song intersect with details of urban journeys to point up the sharply variegated and unequal terrain of the twentieth century metropolis. In Part II, I examine Paul Auster‘s and Orhan Pamuk's postmodern city novels of the 1980s, which diverge from the experimental realism Dos Passos and Tanpınar adopted in the 1920s and 1930s. The economic transformation that both cities underwent from the 1950s on increasingly served to undermine the coordinates of historical memory within the new urban environment, widening the subjective gap between past and present. In this context, I argue that the conflict between the apparent freedoms of globalization and the increasing entrapment of the postmodern subject constitutes the main dilemma of postmodern aesthetics. Auster's City of Glass and Pamuk's The Black Book register this postmodern dilemma in their respective forms through recourse to the metaphor of the 'city as illegible text' and to the broken signifying systems of postmodern allegory. Focusing on these two literary techniques, I examine their differential appropriations in the core and the periphery of the world literary system in order to gauge how the experience of urban modernity – as shaped by particular cultural, social and economic developments – contributes in turn to the shaping of literary form.